Seasons & Episodes
E=mc2
Ruby Jade has to compete with a charming bartender on a date. Josh tries to keep control of his classroom as people star
Orion
Josh's students compete for an invite to the exclusive and elusive dating app, Orion. Ruby has near success at the dog p
Threesome
Thanks to a new dating app, Ruby has the most interesting sex of his life. Josh allows Ruby to regale the class with his
Goodnight
Ruby desperately tries to extend his date with Martha. Martha imparts some harsh wisdom. Guest Starring: Nikki Taguilas-
French
Josh runs into Ruby and gives him the surprise of his life. Unraveling, Ruby spirals into an impromptu date with a drive
Pool Party
Ruby prepares his home for what he's hoping will be the event of a lifetime. Josh tries to make peace with Ruby. Guest
Lines
Ruby attempts to get in shape by hiring a personal trainer. Back in class he practices pickup lines on Ivan. Guest Starr
Topless Maid
Ruby hires an exciting cleaning service, but things don't go as he fantasized. Josh tries to keep Ruby from disrupting t
Open Mic
Ruby flexes his comedy muscles on a date. Josh then helps Ruby break down exactly what went wrong. Guest Starring: Katie
Orion Part II
Ruby finally hears back from Orion. The decision changes both Ruby and Josh's his life forever. Cast: Kristen Brancaccio
Mini Master
Ruby Jade is back and wants to return to Josh's class, if not as a student, then as a teacher's assistant.
Salsa Sarah
Ruby learns that the dating climate has changed in the last few years and uses his newfound knowledge on an artisan sals
The Groomsmen
Ivan and his groomsmen try on their tuxedos for the big day. Ruby plays a nasty prank on Ivan.
Game Night
After a strange hypnotherapy session, Ruby spends 'game night' trying to cozy himself up to his date's friends.
A Tale of Two Evenings
After a strange hypnotherapy session, Ruby spends 'game night' trying to cozy himself up to his date's friends.
Escape Room
Ruby attempts to impress his date with his intellect as they try to navigate an escape room.
Bachelor Party
Ivan's bachelor party is in full swing when Ruby considers this his time to shine.
Dance Off
Ruby and Raj square off in a series of escalating feats of stupidity.
The Wedding
Ruby has a huge crush on somebody at Ivan's wedding but doesn't know how to let her know.
The Decision
Ruby makes the biggest decision of his life.
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